Methyl iodide → HCID 178503480, compound

HRID 1721872Notes

Reaction equation

HRID 1721872 reaction equation
[CH3:1][C:2]([NH:5][S:6]([C:9]1[C:10](=[O:16])[NH:11][C:12](=[S:15])[NH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].[CH3:17]I>CN(C=O)C>[CH3:4][C:2]([NH:5][S:6]([C:9]1[C:10]([OH:16])=[N:11][C:12]([S:15][CH3:17])=[N:13][CH:14]=1)(=[O:7])=[O:8])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 6328Methyl iodide3×HCID 19860383HCID 19860383, compound

Product 1

HCID 178503480HCID 178503480, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(1,1-Dimethylethyl)-1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-pyrimidinesulfonamide (30.69 g, 116.7 mmol) was dissolved in DMF (300 mL) and methyliodide was added (8.72 mL, 140 mmoles) and the mixture was stirred at ambient temperature for 24 hours. An additional quantity of methyliodide (2.5 mL) was added and the reaction stirred an additional 24 hours. A final addition of methyliodide (2.0 mL) was made followed by another 24 hours of stirring to complete the reaction. The DMF was removed under reduced pressure, the residue was suspended in water (300 mL), sodium carbonate was added until the solution was neutralized, then the pH was adjusted to 8 with sodium hydroxide pellets. The aqueous solution was filtered, extracted with three 150 mL portions of ethyl acetate. The pH of the aqueous portions was adjusted to 3 with 37% HCl, the white solid that precipitated out was filtered, washed with water, and dried in a vacuum oven to yield 20.16 gm (72.78 mmol, 62%) of product which was used as is in the next step. An analytical sample crystallized from ethanol/water, had a m.p. 225.5° C.

Workup

  1. stirringthe reaction stirred an additional 24 hours
  2. waitwas made followed by another 24 hours
  3. stirringof stirring
  4. customthe reaction
  5. customThe DMF was removed under reduced pressure
  6. additionsodium carbonate was added until the solution
  7. filtrationThe aqueous solution was filtered
  8. extractionextracted with three 150 mL portions of ethyl acetate
  9. customthe white solid that precipitated out
  10. filtrationwas filtered
  11. washwashed with water
  12. customdried in a vacuum oven

Sources & evidence

ORD record
ord-58c2bca9f80e4ac699f472ff4b7585b2
Source dataset
uspto-grants-1989_08
Patent number
US04853389

Reaction notes

Loading…